EP0542973B1 - Pflanzenschutzmittel, verfahren zu seiner herstellung und sein gebrauch, insbesondere zur unkrautbekämpfung - Google Patents

Pflanzenschutzmittel, verfahren zu seiner herstellung und sein gebrauch, insbesondere zur unkrautbekämpfung Download PDF

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EP0542973B1
EP0542973B1 EP92912285A EP92912285A EP0542973B1 EP 0542973 B1 EP0542973 B1 EP 0542973B1 EP 92912285 A EP92912285 A EP 92912285A EP 92912285 A EP92912285 A EP 92912285A EP 0542973 B1 EP0542973 B1 EP 0542973B1
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Prior art keywords
cyclodextrin
plant protection
composition according
benzamide compound
derivatives
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English (en)
French (fr)
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EP0542973A1 (de
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Serge Gosset
Christian Gauvrit
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Roquette Freres SA
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Roquette Freres SA
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2

Definitions

  • the present invention relates, as new industrial products, phytosanitary compositions based on benzamide compound (s) and cyclodextrin (s), useful in particular for the protection of plants against undesirable plant species.
  • compositions and their use, post- and / or pre-emergence of the plants to be protected.
  • the present invention relates very particularly to the preparation of phytosanitary compositions containing, as a benzamide compound with a herbicidal vocation, N- [3- (1-ethyl-1-methylpropyl) -5-isoxazolyl] -2,6-dimethoxybenzamide , also known as "Isoxaben", and their use for the protection of crops, especially cereals.
  • plants in particular all the plant species cultivated by man, in particular those intended for its food or that of the animal (cereals, fodder crops, vegetables, fruit trees, vines, etc.), and / or to the supply of wood from all destinations (heating, construction of housing, furniture, etc.) and / or to ornamentation (forest, ornamental, floral crops, grass, etc.).
  • undesirable plant species are meant those which adversely affect the intended use or uses of cultivated plants and in particular those whose presence adversely affects in a qualitative and / or quantitative manner, the growth and / or the harvest of all or part of cultivated plants.
  • This definition includes all plant species qualified, in common parlance, as "weeds", in particular those belonging to the dicotyledonous class.
  • This mobility is obviously influenced by the intrinsic chemical nature of the herbicide but also by external factors linked, among other things, to the physicochemical nature and the humidity of the substrate.
  • JAMET et al have shown that herbicides such as the products known under the respective names of "Metamitron” and “Atrazine”, exhibit different mobility, expressed according to the five-class classification of HELLING and TURNER, according to the nature of the soil to which they were applied (Bull. Environ. Contam. Toxicol. (1988), 41: 135-142.
  • Atrazine is classified, for example, as “immobile” (class 1) in certain substrates and “not very mobile” (class 2) or “moderately mobile” (class 3) in others.
  • JAMET showed that a benzamide herbicide such as N- [3- (1-ethyl-1-methylpropyl) -5-isoxazolyl] -2,6-dimethoxybenzamide, also known under the name "Isoxaben ", could be considered perfectly immobile (class 1), regardless of the nature of the substrate to which it was applied.
  • Isoxaben is more particularly used as a pre-emergent herbicide for the protection of winter cereals such as common wheat, durum wheat, barley, oats, triticale or rye.
  • Isoxaben is likely to apply to any benzamide compound with a herbicidal vocation whose mobility and / or effectiveness is potentially or effectively insufficient in such a context, in particular those of qualifying as “immobile” or “not very mobile” in the substrate (s) intended to support the targeted crops.
  • the subject of the present invention is a phytosanitary composition, useful in particular for the protection of plants against undesirable plant species, characterized in that it contains at least one benzamide compound associated with at least one cyclodextrin so as to improve mobility in the soil and / or the biological efficiency of said benzamide derivative and in that the molar ratio between cyclodextrin (s) on the one hand and benzamide compound (s) on the other hand is at most equal to 2/1.
  • the present invention is all the more surprising and unexpected in character as investigations specifically targeting the screen simulation, by computer-aided modeling, of molecular systems between cyclodextrins and different active principles, have shown that Isoxaben and beta-cyclodextrin could not be subject to real inclusion complexes, unlike other active ingredients studied (Minutes, 5th Int. Symposium on Cyclodextrins, 28-30 March 1990, p. 101-106).
  • benzamide compound means any compound capable of having, among other functions, a herbicidal function and which corresponds to the general formula below: in which Z is an oxygen or sulfur atom.
  • the groups R1 to R6, which may be identical or different, are in particular of the hydrogen, halogen, alkyl, including hydroxy, halo or thioalkyl, alkenyl, alkoxy, in particular methoxy or ethoxy, or aryl, type.
  • aryl is in no way limiting, in particular in its application to the group R6 and the general formula given above must be understood as including, inter alia, the N-arylbenzamide compounds described in the patent EP -B-0 049 071, in particular from line 17 on page 1 to line 55 on page 12.
  • cyclodextrin means any macrocycle constructed from six, seven or eight glucose units and designated respectively by alpha, beta or gamma cyclodextrin, as well as any derivative of any of these.
  • derivative should be understood to include any macrocycle as just defined for which at least one of its constituent glucose units is substituted, at least in one place, by a 'group or a molecule which can be of very diverse size and functionality, such as for example an alkylated and in particular hydroxyalkylated group such as a hydroxypropyl group or for example a mono- or di-saccharide molecule such as a maltose, glucose, fructose or sucrose molecule .
  • a cyclodextrin chosen from the group comprising beta-cyclodextrin and its derivatives, alpha-cyclodextrin and its derivatives, as well as any mixtures of at least any two are used. of these products.
  • Said mixtures may, by way of example, jointly contain and in variable proportions, each of the three types of cyclodextrins mentioned above (alpha, beta and gamma) as well as, optionally, other constituents such as linear dextrins and / or d 'other more or less complex saccharide structures.
  • the cyclodextrin typically used in the compositions according to the invention consists essentially of beta-cyclodextrin and / or one of its derivatives, in particular hydroxyalkylated.
  • the phytosanitary compositions according to the invention have, surprisingly, maximum effectiveness for the low molar ratios cyclodextrin (s) / benzamide compound (s).
  • this molar ratio is more particularly between 0.1 / 1 and 1/1.
  • compositions may be in very diverse solid or liquid forms and, for example, in the form of wettable powders, concentrated suspensions, slurries, aerosols, powders for dusting or dispersion, solutions, concentrates soluble in l , emulsifiable concentrates, emulsions, etc.
  • compositions do not in any way prevent them from being adjuvanted with the aid of the products usually used in formulation such as in particular support agents, diluents or solvents, surfactants, dispersing agents, emulsifying agents, antifreeze agents, dyes.
  • the Applicant Company has also demonstrated the possibility of advantageously using xanthan gum as an adjuvant, and in particular a dispersing agent, of said compositions.
  • the phytosanitary compositions according to the invention may contain, in addition to the benzamide compound (s), one or more other active materials, in particular for herbicide, fungicide, insecticide, nematicide or bactericide purpose.
  • the active ingredient benzamide may be combined in variable proportions with one or more other herbicides of all kinds other than benzamide, and in particular chosen from the group comprising triazines, triazoles, diazines, toluidines, urea derivatives, sulfonylureas, benzonitriles, amides, benzoic, phalic, picolinic or phenolic derivatives, and carbamates.
  • the herbicide which can be combined with the active ingredient benzamide will be chosen from the group comprising the products known under the names of Diuron, Méthabenzthiazuron, Isoproturon, Linuron, Chlortoluron, Ametryne, Simazine, Trifluraline, Terbutryne, Propyzamide, Oxadiazon, Napropamide, Metazachlore, Alachlore and Prosulfocarb.
  • compositions according to the invention As regards the method of preparing the compositions according to the invention, this remains simple and does not in any way require the use of apparatus and other technical means of implementation which is expensive and / or delicate. However, care should be taken to ensure that this preparation is carried out under conditions ensuring at best the obtaining of an intimate mixture between cyclodextrin (s) and benzamide compound (s).
  • a cyclodextrin in particular beta-cyclodextrin
  • a composition of pre-formulated herbicidal material already existing on the market such as for example the formulation called "Cent- 7 "based on Isoxaben sold by the company DOW ELANCO as will be exemplified elsewhere.
  • cyclodextrin Commercial formulations to which cyclodextrin will be added may obviously combine, in variable proportions, a benzamide compound such as Isoxaben and at least one other non-benzamide herbicidal active material such as those mentioned above.
  • formulations may in particular be those marketed by DOW ELANCO under the names “Aubaine”, “Ixo-7”, “Sextan”, “Crescendo”, “Snapshot” or “Flexidor”, by CIBA-GEIGY under the names “Fanfare” or “Cibral” or by BAYER under the name “Glytex”.
  • a process for the preparation of a phytosanitary composition useful in particular for the protection of cultivated plants against undesirable plant species characterized in that it comprises a step during which one brings into contact one of the other, in the presence or absence of third constituents, at least one benzamide compound with a herbicidal vocation and at least one cyclodextrin, the cyclodextrin (s) / benzamide compound (s) molar ratio being at most equal to 2/1.
  • compositions according to the invention make it possible, as will be exemplified below, to surprisingly improve the effectiveness of said benzamide compounds and thereby to allow, with regard to the compositions of the prior art, to under-dose these active ingredients without affecting the effectiveness of the phytosanitary treatment.
  • cyclodextrins are derived from renewable plant materials, namely starchy materials, and their biodegradability and non-toxicity make them products which are perfectly tolerated by the environment.
  • compositions according to the invention are particularly necessary for the protection of cultivated plants which, like corn, require weeding between May and the end of summer, it is clear that these can, from in general, be advantageously used to protect all the crops which, at a given time, must be cleared of all or part of the weeds present, in particular those of the dicotyledon class, and in particular be applied to all of the cereal crops (common wheat, durum wheat, barley, oats, triticale, rye, barley), vineyard and ornamental trees and shrubs (conifers for example).
  • cereal crops common wheat, durum wheat, barley, oats, triticale, rye, barley
  • vineyard and ornamental trees and shrubs (conifers for example).
  • compositions according to the invention there may be mentioned, without this list being limiting, the undesirable plant species belonging to the families of chenopodiaceae, amarantaceae, cruciferaceae or Solanaceae.
  • compositions according to the invention containing Isoxaben as a benzamide compound, the latter possibly being able to be combined with other herbicidal active ingredients.
  • compositions according to the invention combining a cyclodextrin, in particular beta-cyclodextrin sold by the Applicant Company under the name KLEPTOSE R B, and Isoxaben as a compound benzamide, the latter being used as such or in the form of a composition of preformulated herbicidal material (product "CENT-7" sold by the company DOW ELANCO).
  • a cyclodextrin in particular beta-cyclodextrin sold by the Applicant Company under the name KLEPTOSE R B
  • Isoxaben as a compound benzamide
  • dose N the generally recommended dose for Isoxaben, at least for the protection of cereals, is 125 g per hectare (dose hereinafter referred to as dose N).
  • Preparations not in accordance with the invention namely not typically containing cyclodextrin, were obtained by using respectively 125 and 250 microliters of formulation CENT-7 in one liter of water.
  • preparations T1 and T2 respectively, correspond respectively to the doses N / 16 and N / 8 mentioned above.
  • compositions according to the invention hereinafter designated I1 and I2 respectively, were prepared in the same way except that it was used, together with the formulation CENT-7 in the proportions described above , respectively 0.16 and 0.32 g / l of beta-cyclodextrin KLEPTOSE R B.
  • compositions according to the invention I1 and I2 are dosed respectively in Isoxaben at N / 16 and N / 8 and each have a molar cyclodextrin / benzamide compound ratio of 6/1.
  • pre-germinated amaranth Amaranthus albus
  • nightshade Solanum nigrum
  • crops pre-germinated amaranth and nightshade seeds are used as undesirable plant species. It should be remembered that nightshade is a weed that can colonize, among other things, corn.
  • the seeds are put to pre-germinate on petri dishes containing gibberellic acid GA310 ⁇ 4M.
  • the nightshade seeds are subjected, in an air-conditioned enclosure, to an alternation of 16 h of light at 25 ° C and 8 h of darkness at 20 ° C, until germination.
  • amaranth seeds are placed for 16 h in the light at 22 ° C and 8 h in the dark at 14 ° C.
  • Plastic pots are filled with 400 grams of a mixture of earth (2/3) and sand (1/3) sieved to 2 mm. They are adjusted to grams for 50% of field capacity (CC) and 480 grams for 100% of CC, this notion of field capacity or retention capacity corresponding to the maximum water that the soil can retain under conditions where its drainage is freely assured.
  • CC field capacity
  • the preparations T1, T2, I1 and I2 are stirred for 30 minutes then the pots are treated using a sprayer (pressure: 2 bars).
  • the results are evaluated by harvesting, at the stage where the aerial part of the control plants (untreated) has 2 true leaves, then placed in the oven at 80 ° C. for 24 hours, the aerial parts obtained for each treatment. A weighing gives the weight of dry matter thus recovered.
  • This protocol is only implemented on nightshade and in soil moistened to 100% of its capacity in the field.
  • the pots contain 30 nightshades which have not undergone a pre-germination and are covered with a film of earth.
  • the experiment involves five repetitions.
  • the plants are harvested at the 4 true leaf stage of the control. The evaluation of the results is done in accordance with protocol A. In addition, the percentage of weed emergence obtained is noted.
  • results are expressed as a percentage inhibition of the growth of the target weed, this percentage being determined by the formula below: untreated control weight - test weight untreated control weight x 100 the weights being those obtained after passage through the oven as described above.
  • Table I shows the% growth inhibition obtained as a function of the target weed (amaranth, nightshade), of the herbicide preparation tested (preparations T1 and T2 not in accordance with the invention, compositions I1 and I2 in accordance with the invention), of the protocol used (protocols A and B) and for protocol A, of the capacity in the field tested (50 or 100%).
  • compositions according to the invention I1 and I2 can be validly used as herbicidal compositions, in particular when the benzamide compound is used in the form of a composition of pre-formulated herbicidal material.
  • compositions tested which have a high cyclodextrin / benzamide compound molar ratio (6/1) do not in all cases make it possible to obtain results significantly different from those obtained with the control preparations T1 and T2 which exhibit the same concentration of benzamide herbicide.
  • the cyclodextrin used in the compositions according to the invention is the beta-cyclodextrin KLEPTOSE R B sold by the Applicant Company.
  • the benzamide compound (Isoxaben) is used as such or provided in the form of preparation CENT-7.
  • the dose used in Isoxaben, for all of the preparations tested (control preparations or in accordance with the invention) is the dose N / 16 defined above.
  • the tests take place in an air-conditioned enclosure in alternating 16 hours of light (temperature 22 ° C, relative humidity 60%) and 8 hours of darkness (14 ° C, 80%).
  • the pots are daily brought back to the water content corresponding to the retention capacity in the field.
  • Protocol A implementation of Isoxaben as such
  • Protocol B implementation of Isoxaben in preformulated form
  • Preparations are obtained by using CENT-7 in water at the rate of 125 microliters CENT-7 / l and thus, dosed in Isoxaben at N / 16.
  • Nightshade seeds are put to germinate on wet paper in an alternation 16 hours of light (temperature 25 ° C), and 8 hours of darkness (20 ° C).
  • the germinated seeds are planted (3 x 10 per method) in pots filled with a mixture (sieved to 2 mm) earth / sand (2/1) adjusted in water to the capacity of retention in the field.
  • the earth contains 32% clay and 2.3% organic matter.
  • the test is placed in the air-conditioned enclosure. When the control plants reach the 2 true leaf stage, the aerial parts are harvested and placed in an oven at 80 ° C. for 24 h to determine the weight of dry matter.
  • All the tests include 3 repetitions, a control and a CENT-7 reference at the same dose / ha as the Isoxaben contained in the preparations according to the invention.
  • Figure 1 attached shows the number of emergencies obtained for the target weed (nightshade) as a function of the beta-cyclodextrin / Isoxaben ratio of the herbicide preparation tested.
  • the preparations tested are dosed at N / 16 in Isoxaben, the latter being supplied in CENT-7 form (cf. protocol B above-described).
  • the abscissa point 0 shows the number of tricks obtained for the control preparation CENT-7, not containing cyclodextrin.
  • compositions according to the invention are, in terms of number of weed emergence, at least as effective as the preparation free of cyclodextrin.
  • Figure 2 appended shows the growth of the target weed (nightshade), expressed in mg / plant as a function of the beta-cyclodextrin / isoxaben ratio of the herbicide preparation tested.
  • the abscissa point 0 shows the growth obtained for the control preparation CENT-7, not containing cyclodextrin.
  • a control test for which the nightshade has not undergone any herbicide treatment shows that, in this case, the growth of the nightshade is approximately 23 mg / plant.
  • FIG. 2 confirms that all of the compositions according to the invention tested can be validly used as herbicide phytosanitary products.
  • cyclodextrin in particular beta-cyclodextrin, for cyclodextrin / benzamide compound ratios lower than the molar ratio approximately 2/1, makes it possible to achieve an efficiency significantly greater than that of the control preparation free of cyclodextrin, in terms of inhibition of the average growth of the target species.
  • compositions according to the invention prepared according to the protocol A described above made it possible to draw the same conclusions as above, in particular as regards the interest of compositions having a beta-cyclodextrin / benzamide compound molar ratio of between 0.125 / 1 and about 1/1.
  • such compositions have made it possible to reduce from 2/3 to 4/5 approximately the growth of the target weed (nightshade).
  • compositions according to the invention are tested on rapeseed ( Brassica napus ), the peculiarity of which is that it germinates relatively deeply with regard to what happens for nightshade. Herbicides with low mobility in the soil will therefore have even more difficulty in reaching it effectively.
  • this deep germination has the advantage of escaping the possible light stimulus which can in a context of low dosage promote the emergence of the weed.
  • the growing conditions are 16 h of light at a temperature of 19 ° C and a humidity of 60% and 8 h of darkness at 9 ° C and 80%.
  • the pots are daily brought back to the water content corresponding to the retention capacity in the field.
  • the experimental conditions are identical to those described above for nightshade, apart from the number of seeds sown (3 x 33), the soil / sand ratio (1/2) and the growing conditions. (described above).
  • Figure 3 appended shows the number of emergencies obtained for the target weed (rapeseed) as a function of the beta-cyclodextrin / isoxaben ratio of the herbicide preparation tested.
  • compositions according to the invention which can, as in the present case, consist of simple formulations associating mainly cyclodextrin, benzamide compound, water and dispersing agent (xanthan gum).
  • compositions according to the invention having a cyclodextrin / benzamide compound ratio of less than 2/1 and in particular of between 1/1 and 0.125 / 1 approximately appear to be significantly more effective than a fully formulated control herbicidal composition.

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Claims (17)

  1. Pflanzenschutz-Zusammensetzung, die insbesondere zum Schützen von Pflanzen gegen unerwünschte Pflanzenarten geeignet ist, dadurch gekennzeichnet, daß sie mindestens eine Benzamid-Verbindung in Kombination mit mindestens einem Cyclodextrin enthält, um die Mobilität im Erdboden und/oder die biologische Wirksamkeit des genannten Benzamid-Derivats zu verbessern, und daß das Molverhältnis zwischen dem(den) Cyclodextrin(en) einerseits und der(den) Benzamid-Verbindung(en) andererseits höchstens 2:1 beträgt.
  2. Pflanzenschutz-Zusammensetzung nach Anspruch 1, dadurch gekennzeichnet, daß das Molverhältnis vorzugsweise zwischen 0,1:1 und 1:1 liegt.
  3. Pflanzenschutz-Zusammensetzung nach einem der Ansprüche 1 und 2, dadurch gekennzeichnet, daß die Benzamid-Verbindung eine N-Arylbenzamid-Verbindung, insbesondere eine N-Aryl-alkoxy-benzamid-Verbindung, ist.
  4. Pflanzenschutz-Zusammensetzung nach Anspruch 3, dadurch gekennzeichnet, daß es sich bei der N-Aryl-alkoxy-benzamid-Verbindung handelt um N-[3-(1-Ethyl-1-methylpropyl)-5-isoxazolyl]-2,6-dimethoxybenzamid oder Isoxaben oder eines seiner Salze.
  5. Pflanzenschutz-Zusammensetzung nach einem der Ansprüche 1 bis 4, dadurch gekennzeichnet, daß die Benzamid-Verbindung als solche ein im Erdboden unbewegliches oder wenig bewegliches Produkt ist.
  6. Pflanzenschutz-Zusammensetzung nach einem der Ansprüche 1 bis 5, dadurch gekennzeichnet, daß das Cyclodextrin ausgewählt wird aus der Gruppe, die umfaßt β-Cyclodextrin und seine Derivate, α-Cyclodextrin und seine Derivate sowie beliebige Gemische von mindestens zwei beliebigen dieser Produkte.
  7. Pflanzenschutz-Zusammensetzung nach Anspruch 6, dadurch gekennzeichnet, daß das Cyclodextrin im wesentlichen besteht aus β-Cyclodextrin und/oder einem seiner Derivate, insbesondere einem seiner Hydroxyalkyl-Derivate.
  8. Pflanzenschutz-Zusammensetzung nach einem der Ansprüche 1 bis 7, dadurch gekennzeichnet, daß sie außerdem enthält mindestens ein Adjuvans, ausgewählt aus der Gruppe, die umfaßt Trägermittel, Verdünnungsmittel, Lösungsmittel, Dispergiermittel, oberflächenaktive Mittel, Emulgiermittel, Antigelierungsmittel, Färbemittel und/oder mindestens ein aktives Material, ausgewählt aus der Gruppe, die umfaßt Herbizide vom Nicht-Benzamid-Typ, Fungizide, Insektizide, Nematozide und Bakterizide.
  9. Pflanzenschutz-Zusammensetzung nach Anspruch 8, dadurch gekennzeichnet, daß das aktive Material (der Wirkstoff) ein Herbizid vom Nicht-Benzamid-Typ ist, das ausgewählt wird aus der Gruppe, die umfaßt Triazine, Triazole, Diazine, Toluidine, Harnstoffderivate, Sulfonylharnstoffe, Benzonitrile, Amide, Benzoesäure-Derivate, Phthalsäurederivate, Picolinsäurederivate, Phenolderivate und Carbamate, und das insbesondere ausgewählt wird unter den Produkten, die unter den Bezeichnungen Diuron, Metabenzthiazuron, Isoproturon, Linuron, Chlortoluron, Ametryn, Simazin, Trifluralin, Terbutryn, Propyzamid, Oxadiazon, Napropamid, Metazachlor, Alachlor und Prosulfocarb bekannt sind.
  10. Zusammensetzung nach einem der Ansprüche 8 oder 9, dadurch gekennzeichnet, daß sie Xanthan-Gummi enthält.
  11. Pflanzenschutz-Zusammensetzung nach einem der Ansprüche 1 bis 10, dadurch gekennzeichnet, daß sie weniger als etwa 125 g/l, insbesondere 5 bis 120 g/l, Benzamid-Verbindung(en) enthält.
  12. Verfahren zur Herstellung einer Pflanzenschutz-Zusammensetzung, die insbesondere zum Schützen von Pflanzen gegen unerwünschte Pflanzenarten verwendbar ist, dadurch gekennzeichnet, daß es eine Stufe umfaßt, in deren Verlauf man in Gegenwart oder Abwesenheit dritter Bestandteile miteinander in Kontakt bringt mindestens eine Benzamid-Verbindung als Herbizid, insbesondere Isoxaben, und mindestens ein Cyclodextrin, insbesondere β-Cyclodextrin, wobei das Molverhältnis zwischen Cyclodextrin(en) und Benzamid-Verbindung(en) unterhalb 2:1, vorzugsweise zwischen 0,1:1 und 1:1, liegt.
  13. Verfahren nach Anspruch 12, dadurch gekennzeichnet, daß in der genannten Stufe die Benzamid-Verbindung in Form einer vorformulierten Herbizidmaterial-Zusammensetzung eingesetzt wird.
  14. Verfahren zur Pflanzenschutz-Behandlung, insbesondere zum Schützen von Pflanzen gegen unerwünschte Pflanzenarten, dadurch gekennzeichnet, daß man nach und/oder vor dem Auflaufen der zu schützenden Pflanzen eine Pflanzenschutz-Zusammensetzung nach einem der Ansprüche 1 bis 11, oder hergestellt nach den Ansprüchen 12 oder 13, verwendet, wobei die Zusammensetzung vorzugsweise auf die Oberfläche und/oder in das Innere des Substrats angewendet wird, das dazu bestimmt ist, die Pflanzen zu tragen oder das die Pflanzen trägt.
  15. Verfahren zur Pflanzenschutz-Behandlung nach Anspruch 14, dadurch gekennzeichnet, daß die zu schützenden Pflanzen ausgewählt werden aus der Gruppe von Getreide, insbesondere Mais und Wintergetreide, Wein und Zier-Bäumen und -Sträuchern, insbesondere den Koniferen.
  16. Verfahren zur Pflanzenschutz-Behandlung nach einem der Ansprüche 14 und 15, dadurch gekennzeichnet, daß sämtliche oder ein Teil der unerwünschten Pflanzenarten Dicotyledonen sind und insbesondere den Familien der Chenopodiazeen, der Amarantazeen, der Cruciferazeen und der Solanazeen angehören.
  17. Verfahren zur Pflanzenschutz-Behandlung nach einem der Ansprüche 14 bis 16, dadurch gekennzeichnet, daß man vor dem Auflaufen der zu schützenden Pflanzen eine Zusammensetzung verwendet, die β-Cyclodextrin und Isoxaben enthält.
EP92912285A 1991-06-10 1992-06-10 Pflanzenschutzmittel, verfahren zu seiner herstellung und sein gebrauch, insbesondere zur unkrautbekämpfung Expired - Lifetime EP0542973B1 (de)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
FR9107012A FR2677221B1 (fr) 1991-06-10 1991-06-10 Composition phytosanitaire, son procede de preparation et son utilisation, en particulier pour lutter contre les mauvaises herbes.
FR9107012 1991-06-10
PCT/FR1992/000520 WO1992022204A1 (fr) 1991-06-10 1992-06-10 Composition phytosanitaire, son procede de preparation et son utilisation, en particulier pour lutter contre les mauvaises herbes

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EP0542973A1 EP0542973A1 (de) 1993-05-26
EP0542973B1 true EP0542973B1 (de) 1996-01-17

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US (1) US6037311A (de)
EP (1) EP0542973B1 (de)
JP (1) JPH06500572A (de)
AT (1) ATE133031T1 (de)
CA (1) CA2089142A1 (de)
DE (1) DE69207728D1 (de)
FR (1) FR2677221B1 (de)
HU (1) HUT62764A (de)
WO (1) WO1992022204A1 (de)

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WO2001097613A2 (en) * 2000-06-23 2001-12-27 Basf Aktiengesellschaft Enhancement of the activity of carotenoid biosynthesis inhibitor herbicides
US6894003B2 (en) 2000-06-23 2005-05-17 Basf Aktiengesellschaft Enhancement of the activity of carotenoid biosynthesis inhibitor herbicides
UA78071C2 (en) * 2002-08-07 2007-02-15 Kumiai Chemical Industry Co Herbicidal composition

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MA19269A1 (fr) * 1980-09-16 1982-04-01 Lilly Co Eli Perfectionnement relatif a des derives de n-arylbenzamides .
GB2162529B (en) * 1984-06-08 1988-03-02 Nitrokemia Ipartelepek B-cyclodextrin complex of benzene sulphonyl urea derivatives
JPS6379802A (ja) * 1986-09-24 1988-04-09 Nippon Nohyaku Co Ltd サイクロデキストリンを含有する農薬組成物

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DE69207728D1 (de) 1996-02-29
JPH06500572A (ja) 1994-01-20
FR2677221B1 (fr) 1993-10-15
HU9300333D0 (en) 1993-05-28
CA2089142A1 (fr) 1992-12-11
WO1992022204A1 (fr) 1992-12-23
HUT62764A (en) 1993-06-28
FR2677221A1 (fr) 1992-12-11
EP0542973A1 (de) 1993-05-26
US6037311A (en) 2000-03-14
ATE133031T1 (de) 1996-02-15

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